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Substance Name: Tetradecanoylphorbol acetate
RN: 16561-29-8
UNII: NI40JAQ945
InChIKey: PHEDXBVPIONUQT-RGYGYFBISA-N

Note

  • A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.

Molecular Formula

  • C36-H56-O8

Molecular Weight

  • 616.8304
 

Classification Codes

  • Carcinogens
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Names and Synonyms

Results Name

  • Tetradecanoylphorbol acetate

Name of Substance

  • 12-O-Tetradecanoylphorbol-13-acetate
  • Tetradecanoylphorbol acetate

MeSH Heading

  • Tetradecanoylphorbol acetate

Synonyms

  • 12-O-Tetradecanoyl phorbol acetate
  • 12-O-Tetradecanoylphorbol 13-acetate
  • 12-O-Tetradecanoylphorbol-13-acetate
  • 12-o-Tetradekanoylphorbol-13-acetat
  • 12-O-Tetradekanoylphorbol-13-acetat [German]
  • 12-Tetradecanoylphorbol 13-acetate
  • 12-Tetradecanoylphorbol 13-monoacetate
  • 12-Tetradecanoylphorbol-13-acetate
  • 13-O-Acetylphorbol 12-myristate
  • 13-Tetradecanoylphorbol acetate
  • 4beta-Phorbol 12-myristate 13-acetate
  • 4beta-Phorbol-12-myristate-13-acetate
  • 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-beta-tetramethyl-, 9a-acetate 9-myristate
  • beta-Phorbol 12-myristate 13-acetate
  • BRN 2407201
  • CCRIS 716
  • Factor A1
  • Factor A1 (croton oil)
  • HSDB 3542
  • Myristic acid, 9-ester with 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one 9a-acetate, (+)-
  • NSC 262244
  • Pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
  • Phorbol 12-myristate 13-acetate
  • Phorbol 12-tetradecanoate 13-acetate
  • Phorbol acetate, myristate
  • Phorbol ester
  • Phorbol monoacetate monomyristate
  • Phorbol myristate acetate
  • Phorbol-12-myristate 13-acetate
  • Phorbol-12-myristate-13-acetate
  • Phorbol-myristate acetate
  • PMA
  • PMA (tumor promoter)
  • Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
  • Tetradecanoylphorbol acetate
  • TPA
  • TPA (phorbol derivative)
  • UNII-NI40JAQ945

Systematic Names

  • 12-O-Tetradecanoylphorbol-13-acetate
  • Myristic acid, 9-ester with 1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydro-4a-beta,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alpha-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 9a-acetate
  • Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9, 9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aa,1bb,4ab,7aa,7ba, 8a,9b,9aa))-
  • Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-

Superlist Name

  • 12-O-Tetradecanoylphorbol-13-acetate

Registry Numbers

CAS Registry Number

  • 16561-29-8

FDA UNII

  • NI40JAQ945

Other Registry Numbers

  • 11016-13-0
  • 11019-85-5
  • 20839-11-6
  • 26894-58-6
  • 27534-73-2
  • 51898-14-7

System Generated Number

  • 0016561298

Structure Descriptors

InChI

InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

InChIKey

PHEDXBVPIONUQT-RGYGYFBISA-N

Smiles

CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@@]3(O)[C@H]2C=C(C)C3=O)[C@@H]4C(C)(C)[C@]14OC(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LDLo intravenous 40ug/kg (0.04mg/kg) BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: CHANGES IN PLATELET COUNT
Journal of Applied Physiology. Vol. 54, Pg. 267, 1983.
mouse LD intraperitoneal > 1mg/kg (1mg/kg)   Toxicon. Vol. 38, Pg. 123, 2000.
mouse LD50 intravenous 309ug/kg (0.309mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Agents and Actions, A Swiss Journal of Pharmacology. Vol. 16, Pg. 535, 1985.